Process of producing substances having tanning action



. body and excellent stability to light.

l these examples.

estara im., '5,1942

A raamt l .racsss or raonncma suas'raus i mvmo ranma norton nomma stm,

Sweden, andv E Germany, assignors. by

General me f .rf Film N'ya non, n:

sonnette 'i l] im.

' www' w Corporation, New

York, N. Y., a corporation o3 Delaware" Nonrawmg. Application s aftosa,sessi 1 ew. i El. 17, imi@ No. 260,504. m

' e emma l (c1. ze)

, cording to which sulphonio acids of polynuclear aromatic hydrocarbons,li desired, in admixture with other aromatic sulphonic acids, aretreated with urea and formaldehyde. The resulting products, when theyare insoluble or insuiiicienttion oi coal and ,50

ly soluble, are rendered water-soluble by the action of aromaticsulphonic acids such as phenol sulphonic acids, cresci sulphonic 'acidsoranthracene sulphonic acids and formaldehyde or condensation productsobtainable therefrom.

We have now found that especially valuable products can be obtained byusing omega-methyl sulphonic acids oi aromatic.- advantageouslyhydroxyl-group-cbntaining, poiynuclear compounds in the treatment of thesulphonic acids oi polylnuclear aromatic hydrocarbons ywith urea andformaldehyde according to the first stage oi the said process and/or inthe treatment for the purpose i increasing solubility according to thesecond stage of the said process, together with the 'other aromaticsulphonic acids. As components of the said kind there may be mentionedthe addition products oi formaldehyde bisulphite with4.idihydroxydiphenyl-sulphone or 4.4'di hydroxydicresyl-sulphones ordroxyphenyl) propane, and also with condensation products of phenol andmethyl ethyl ketone. phenol and acetophenone, phenol and cyclohexanone,and ortho-cresci and acetone.

For the rest, the initial materials to be used are the same as in thesaid process, and the workingoonditions are substantially the same.

The products obtainable according to this invention may be used astanning agents either directly or aiter neutralization to a suitabledegree of acidity. They tanning action and. yield white leather of goodThe following examples will further illustrate how vthe said inventionmay be carried out in practice but the invention is not restricted toThe parts are by weight.

Example 1 30 parts oi the addition product of formaldehyde bisulphiteand 4.4'dihydroxydlphenylsul phone and also are distinguished by highvgether with 2id parte oi there are gradually ythus i droxy-phenyl)propane in a solution of s0 parte of crude naphthalene ed `paroi water.At 50 c.

sulphonic acid in there are added 2da parte of a 30 per centformaldehyde solution d then d0 parte oi a sulphonic acid mine obted bysulphonation oi `from the hydrogena parte oi the addition product aphenol ture a of formaldehyde bisulphate and e.a'dihydroxydiphenyl-sulphdne are added.' The mixture is heated at from per centaqueous formaldehyde solution are added and the whole hea at irom6o to70 C. ior in hour. y It is vthen neutralized with 12.5 parte oi soda, ai -fagent bains obtained which yields leather which is very stable toiight and oi goed body. f/

Esempio 2 180 parte ci crude-naphthalene sulphonic acid obtained bysulphonatina naphthalene with an. equal weightbi @a per cent phuricacid), tothe addition product of bisulphate and beta-beta=di hy and. 72parts o urea are parte ci water.- .At 50 C. added 14,5 parts ci 30 percent iormaldehyde, 240 vp of cresol sulphonic acid and 455 parts oi theaddition product of formaldehyde bisulphite and bete.betadi(hy4droxyphenyl) propane. The mixture is heated to 'cooling to 25 (2.,:83parts of 30 per cent formaldehyde are added and the whole heated ior 2hours at irom 60 to '20 formaldehyde dissolved hot` in 180 C. Byneutralization with 106 parts of 25 per cent ammonia, a tannins agent isobtained which yields aleather stable to light.

what we c l ist' i. The process for' the production ci substances havinaaction, which comprises treating a sulphonic acid oi a poiynucleararovvmatic hydrocarbon and an addition product of formaldehydebisulflte' on an pound corresponding to the formula R-X-R wherein each Rstands for a phenyl radical bearing an hydroxyl group and X stands for abridge selected from the group consistina ofl CHt so I a8l1 0\ I C Hswith urea and iormaldehyde and improving the water-solubility oi theproduct obtained by a treatment with 'an addition product oi the arore-nsaid kind d an aromatic sulphonic acid se- 12 parte ci urea aredissolved hot 5d lected from the class consisting oi phenol sul do to @0C., cooled to about 25"l C., i337 parts ci d@ aromatic comv aldehyde.

2. The process for the production of subi stances having tanning action,which comprises w treating a sulphonic acid of a polynuclear aromatichydrocarbon and an addition product of formaldehyde-bisulphite on adihydroxy diaryl sulphone with Aurea and formaldehyde and improving thewater-solubility of the product obtained by a treatment with anadditionproduct oi' formaldehyde-bisulphite on a dihydroxy dii aryl sulphone andwith an aromatic sulphonic acid selected from the class consisting ofphenol sulphonic acids and cresol sulphonic acids and formaldehyde.

3. The process for ,the production of sub l stances having tanningaction, which comprises 1 treating a-sulphonic acid of a polynucleararomatic hydrocarbon and an addition product oi lpi'renyDpropane withurea and formaldehyde and improving the water-solubility of the productobtained by a treatment withan addition 1 product offormaldehyde-bisulphite on -di(hy droxyphenyb propane and with anaromatic sulphonic acid selected from the class consisting of `phenolsulphonic acidsand cresol sulphonic t acids and formaldehyde.

4. Products from the reaction of al-suiphonic acid of a poiynucleararomatic hydrocarbon and an addition product of formaldehyde bisulte onan aromatic compound corresponding to the formula R-X-R wherein each Rstands for `a phenyl radical bearing an hydroxyl groupand vfrom theclass consisting of 2,282,264 phonic acids and cresol sulphonic acidsand form- X stands forv a bridge selected from the group consisting ofCHI urea and formaldehyde, after-treated with an addition droxyphenyl)propane and an aromatic sulphonic acid selected from the classconsisting of phenol sulphonic acids and cresol sulphonic acids andformaldehyde.

. i i EDMUND STIASNY.

HERMANN SCHUETTE.

product ofthe aforesaid kind and an, aromatic sulphonic acid selectedfrom the class consisting of phenol sulphonic acids and cresol

